HRP20210966T1 - Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof - Google Patents

Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof Download PDF

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Publication number
HRP20210966T1
HRP20210966T1 HRP20210966TT HRP20210966T HRP20210966T1 HR P20210966 T1 HRP20210966 T1 HR P20210966T1 HR P20210966T T HRP20210966T T HR P20210966TT HR P20210966 T HRP20210966 T HR P20210966T HR P20210966 T1 HRP20210966 T1 HR P20210966T1
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HR
Croatia
Prior art keywords
compound
formula
synthesis
tetraaza
azulene
Prior art date
Application number
HRP20210966TT
Other languages
Croatian (hr)
Inventor
Benno Rothenhaeusler
René Trussardi
Fabienne Hoffmann-Emery
Urs Schwitter
Jean-Michel Adam
Olaf Grassmann
Thomas Hartung
Frederic Ran
Ralph Diodone
Christophe Pfleger
Bjoern Bartels
Original Assignee
F. Hoffmann - La Roche Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by F. Hoffmann - La Roche Ag filed Critical F. Hoffmann - La Roche Ag
Publication of HRP20210966T1 publication Critical patent/HRP20210966T1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Claims (7)

1. Postupak sinteze spoja formule I, naznačen time, da obuhvaća reakciju spoja formule II ili III sa spojem formule VI [image] .1. The method of synthesis of the compound of formula I, characterized in that it includes the reaction of the compound of formula II or III with the compound of formula VI [image] . 2. Postupak prema patentnom zahtjevu 1, naznačen time, da nadalje obuhvaća reakciju spoja formule XI sa spojem formule III: [image] .2. The process according to patent claim 1, characterized in that it further includes the reaction of the compound of formula XI with the compound of formula III: [image] . 3. Postupak prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da nadalje obuhvaća reakciju spoja formule X sa spojem formule XI ili njegovu farmaceutski prihvatljivu sol u sljedećim koracima: [image] .3. The method according to any one of patent claims 1 to 2, characterized in that it further comprises the reaction of the compound of formula X with the compound of formula XI or its pharmaceutically acceptable salt in the following steps: [image] . 4. Postupak prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da nadalje obuhvaća reakciju spoja formule XV sa spojem formule XI ili njegovu farmaceutski prihvatljivu sol u sljedećim koracima: [image] 4. The method according to any one of patent claims 1 to 2, characterized in that it further comprises the reaction of the compound of formula XV with the compound of formula XI or its pharmaceutically acceptable salt in the following steps: [image] 5. Postupak prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da nadalje obuhvaća reakciju spoja formule XXVI sa spojem formule XI ili njegovu farmaceutski prihvatljivu sol u sljedećim koracima: [image] .5. The method according to any one of patent claims 1 to 2, characterized in that it further comprises the reaction of the compound of formula XXVI with the compound of formula XI or its pharmaceutically acceptable salt in the following steps: [image] . 6. Postupak prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da se spoj formule INT formira kao međuprodukt: [image] INT.6. The process according to any one of claims 1 to 2, characterized in that the compound of the formula INT is formed as an intermediate product: [image] INT. 7. Spoj međuprodukt II ili njegova sol III: [image] II: slobodna baza, III: .2HCl.7. Compound intermediate II or its salt III: [image] II: free base, III: .2HCl.
HRP20210966TT 2013-12-05 2021-06-17 Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof HRP20210966T1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13195864 2013-12-05
EP14805290.5A EP3077396B1 (en) 2013-12-05 2014-12-01 Synthesis of trans-8-chloro-5-methyl-1 -[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crytalline forms thereof
PCT/EP2014/076041 WO2015082370A1 (en) 2013-12-05 2014-12-01 Synthesis of trans-8-chloro-5-methyl-1 -[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crytalline forms thereof

Publications (1)

Publication Number Publication Date
HRP20210966T1 true HRP20210966T1 (en) 2021-09-17

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HRP20210966TT HRP20210966T1 (en) 2013-12-05 2021-06-17 Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof

Country Status (20)

Country Link
US (3) US10246460B2 (en)
EP (1) EP3077396B1 (en)
JP (1) JP6454707B2 (en)
KR (3) KR102384630B1 (en)
CN (1) CN105793263B (en)
AR (1) AR098592A1 (en)
AU (2) AU2014359409A1 (en)
CA (2) CA2931016C (en)
ES (1) ES2875411T3 (en)
HK (1) HK1223918A1 (en)
HR (1) HRP20210966T1 (en)
IL (2) IL245450A0 (en)
MX (1) MX2016006558A (en)
MY (1) MY175464A (en)
NZ (1) NZ720340A (en)
PL (1) PL3077396T3 (en)
SG (1) SG11201604502SA (en)
SI (1) SI3077396T1 (en)
WO (1) WO2015082370A1 (en)
ZA (1) ZA201603304B (en)

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CA2931016C (en) * 2013-12-05 2022-11-01 F. Hoffmann-La Roche Ag Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof
WO2017191117A1 (en) 2016-05-03 2017-11-09 Bayer Pharma Aktiengesellschaft V1a receptor antagonists for use in the treatment of renal diseases
KR20200097702A (en) * 2017-12-08 2020-08-19 에프. 호프만-라 로슈 아게 Pharmaceutical formulation
WO2020139670A1 (en) 2018-12-27 2020-07-02 Teva Pharmaceuticals International Gmbh Solid state forms of balovaptan
WO2023059110A1 (en) 2021-10-06 2023-04-13 주식회사 엘지에너지솔루션 Battery module

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CA1197242A (en) * 1983-03-02 1985-11-26 Jean A. Gauthier Pyrimido¬1,2-a|pyrrolo¬2,1-c|¬1, 4|benzodiazepine-3-carboxylic acid derivatives
ES2277237T3 (en) * 2003-02-19 2007-07-01 Pfizer Inc. USEFUL TRIAZOL COMPOUNDS IN THERAPY.
GB0303852D0 (en) 2003-02-19 2003-03-26 Pfizer Ltd Triazole compounds useful in therapy
GB0400700D0 (en) * 2004-01-13 2004-02-18 Pfizer Ltd Compounds useful in therapy
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US7601715B2 (en) * 2005-06-22 2009-10-13 Bristol-Myers Squibb Company Process for preparing triazole substituted azaindoleoxoacetic piperazine derivatives and novel salt forms produced therein
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CA2931016C (en) * 2013-12-05 2022-11-01 F. Hoffmann-La Roche Ag Synthesis of trans-8-chloro-5-methyl-1-[4-(pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulene and crystalline forms thereof

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Publication number Publication date
KR20160093709A (en) 2016-08-08
WO2015082370A1 (en) 2015-06-11
KR102384630B1 (en) 2022-04-11
CA3142754C (en) 2024-01-02
JP6454707B2 (en) 2019-01-16
AU2019201183B2 (en) 2021-03-04
JP2016539168A (en) 2016-12-15
MY175464A (en) 2020-06-29
IL245450A0 (en) 2016-06-30
MX2016006558A (en) 2016-08-03
SG11201604502SA (en) 2016-07-28
AU2014359409A1 (en) 2016-05-19
RU2018135601A (en) 2018-11-22
CN105793263A (en) 2016-07-20
PL3077396T3 (en) 2021-10-04
AU2019201183A1 (en) 2019-03-14
CA2931016C (en) 2022-11-01
CA2931016A1 (en) 2015-06-11
RU2018135601A3 (en) 2022-05-05
CA3142754A1 (en) 2015-06-11
HK1223918A1 (en) 2017-08-11
US20210284648A1 (en) 2021-09-16
NZ720340A (en) 2020-03-27
SI3077396T1 (en) 2021-08-31
ZA201603304B (en) 2022-05-25
US20190194210A1 (en) 2019-06-27
EP3077396A1 (en) 2016-10-12
NZ759478A (en) 2021-06-25
ES2875411T3 (en) 2021-11-10
US20160280712A1 (en) 2016-09-29
EP3077396B1 (en) 2021-04-21
KR102384608B1 (en) 2022-04-08
KR102384629B1 (en) 2022-04-11
CN105793263B (en) 2019-08-23
US10246460B2 (en) 2019-04-02
AR098592A1 (en) 2016-06-01
US11040977B2 (en) 2021-06-22
IL264891B (en) 2021-02-28
KR20210132745A (en) 2021-11-04
KR20210134985A (en) 2021-11-11

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